


As Though It Were Made for Me

by remi_wolf



Category: Critical Role (Web Series)
Genre: Background Fjord (Critical Role), Dress Up, Dresses, Feminine male character, Fluff, Gen, Minor Fjord/Caleb Widogast, Spoilers episode 78, Tooth-Rotting Fluff, Trans Caleb Widogast, Trans Male Character, caleb didn't seem opposed to wearing jester's dress what do you expect from me?, feminine caleb
Language: English
Status: Completed
Published: 2019-09-25
Updated: 2019-09-25
Packaged: 2020-10-27 20:48:15
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,345
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20766728
Author URL: https://archiveofourown.org/users/remi_wolf/pseuds/remi_wolf
Summary: Jester might have meant the offer to Caleb of one of her dresses as a teasing joke to lighten the mood, but Caleb never actually said that he was opposed to the idea. Even if she had forgotten in the madness that was the rest of the day, Caleb certainly hadn't, and now that they were resting for the evening at the Xhorhaus, he could finally see if Jester could make good on the offer outside the gates of Zadash.





	As Though It Were Made for Me

“Jester? Do you have a moment to talk? I know Beau just went out to the baths, but I wanted to know if I could talk to you.”

Caleb rested his forehead on the door of the inn, trying not to think about how strange it still felt to be back in the Xhorhaus, even if they had been in Zadash earlier in the day. The weeks of travel had been a pleasant change of pace from the constant pressure of the various tasks the Bright Queen set out for them. The Cobalt Soul had been an interesting and sobering experience, but something had stuck out in his head throughout the day, even during all of the research that he had been doing with the others and the subsequent hopscotching they did across the continent. Jester had only said it as a passing comment, but it had stuck out, and he wanted to ask her further about it. His thoughts and anxiety surrounding it continued to swirl around his mind, and he stumbled as Jester finally opened up the door. 

“Oh, Caleb. You know you can always talk to me. What is it about? Did you want to talk about Fjord?” Jester asked, bright and bubbly as ever, and Caleb found a smile crawling onto his face without him even meaning to let it happen, though it turned slightly confused at the last question. 

“Fjord? No, I don’t know why I would like to talk about him. No, it’s about..." Caleb sighed, rubbing the back of his head and trying not to get too frustrated or worried or anything like that. He already had half a mind to just make up something stupid before turning around and disappearing. “You mentioned something about having an extra dress that I could borrow?”

Jester squealed almost immediately, and Caleb winced before looking away, trying not to think too much about this. “I knew you wanted to wear my dress, Caleb! And I am slightly bigger than you, but it shouldn’t be too bad of a fit. I can lace it, like, super tight for you,” she said, already closing the door behind them before running over to her bright-pink haversack. Caleb watched her for a moment before sitting down on the low stool in the corner of the room, trying not to pick too much at the scars on his arms now that they weren’t covered by a jacket or illusion. He should have left his jacket on, rather than pulling off the outer layers of his clothes so that he only wore his shirt with his books pressed against his chest. 

“You do not have to let me wear it, Jester. I was mostly curious if it was something that you had meant seriously when we were outside of Zadash, or if it had only been a joke to try and cheer me up,” Caleb said, tapping his fingers against his chest and the straps of his harness before he started to unbuckle it and pull it off. Jester paused, mouth in a small ‘o’ shape as her eyes widened. She looked at Caleb for a moment with that somewhat shocked appearance before turning back to her bag. 

“Of course I meant it as a joke, silly, but that doesn’t mean that I was not seriously offering it, too. I didn’t think you’d want to, but since you do, that just makes it even better,” she said before sighing and pulling out a dress, and then immediately turning back to the bag to start rummaging around for more. “At least  _ someone _ can appreciate a good dress with me. Beau doesn’t like them at all, and it is very annoying.” 

Caleb chuckled at the thought of Beau in a dress, remembering the way Beau looked like a cat convinced to wear clothes the last time they were in Nicodranas. “I can imagine so. It looks like you are pulling out more than one dress, though. How many do you have?”

“Oh, at least five or six. Two are from Xhorhas, and I picked up the rest of them back when we stopped in Nicodranas. I was getting tired of wearing the same three dresses all of the time,” Jester said, shrugging before pulling out a deep green dress and settling it next to the purple one on the bed. Caleb watched her carefully, trying not to let the anxiety gnawing at his stomach get the better of him. Jester wouldn’t laugh at him, and if he hated it, he could simply ask her not to mention it to anyone and disappear before anyone happened to see him. It would be fine. He could manage to just try a dress on. 

Jester finally pushed the haversack onto the floor, a few things spilling out of the open top of it, and Caleb rolled his eyes before walking over to fix it for her as Jester laid the dresses out better. This close, he could see the two dresses far more easily, and he paused, half-way through his motion of picking up the bag. “Oh. Those are...those are lovely, Jester. You did not need to pick out anything so fancy for me,” he said, turning to carefully feel over the fabric of the purple dress, able to see the slight shimmer and sheen that it had and the iridescence to red in the highlights, though he still couldn’t quite make out much of the details with the way it still lay crumpled on the bed. Three green one, however, already laid out flat, and Caleb’s eye caught on that one as he finally righted the bag before looking at it. Jester had it made of a deep green fabric, and he hummed softly as he felt it between his fingers. It looked almost similar to Jester’s jacket, though it seemed to be fashioned more in golds and greens than greens and silvers. He carefully peeled the layers open, seeing that there were two layers to the dress, with the under layer being an even darker green than the outer layer.

“Oh, that one would look so nice on you. Green always looks so nice with red hair. I thought maybe the purple would look nice, and it’s closer to the Xhorhassian fashion, but the green would look so pretty on you,” Jester said, already bouncing with excitement before Caleb had even really decided on anything or had even properly looked at the dress. Still, the fine swirls of golden embroidery on the underdress looked beautiful, and while he worried that his rough hands might snag on the fine fabric, they simply glided smoothly over the fabric. 

“Do you think that I could try this one on?” he asked, barely able to force his voice to be audible, hand snapping to bring Frumpkin into existence around his neck without thinking to try and ease up some of his discomfort. 

“Of course you can, silly. That’s why I pulled it out,” Jester said, a soft giggle in her voice before she turned back to Caleb. “You do need to get undressed, though. I hope you remembered to keep your smallclothes on today.”

“Of course I remembered, Jester,” Caleb said, rolling his eyes before starting to tug off the last layers of clothes on his body, trying not to think of how it was likely going to look all sorts of stupid and ridiculous on him, especially considering he did have a full head on her, but they were practically just as slight as each other, so perhaps it wouldn’t look too ridiculous on him. He carefully folded and set his clothes aside before glancing back at Jester, trying not to let his nerves show towards her at all. The way she bit her lip and her eyebrows narrowed made it clear that he wasn’t hiding it nearly as well as he thought he did, though the expression on her face quickly disappeared as she smiled at him. 

“It is only a dress, Cay-leb,” she said, drawing his name out in her usual sing-song fashion when she tried to make them all feel better. “I know you probably haven’t worn one before, but they’re not death traps at all.”

Caleb blinked before smiling at her, that same secretly fond smile that he always gave her. “I have worn dresses before. It has just been a very long time,” he said before standing up straighter to look over the dress to try and figure out how exactly this one worked, especially as it seemed that it had some sort of boning within the bodice, cleverly hidden by golden embroidery spinning out spirals and swirls of contrast against the green fabric. 

“Oh. You have? When did you wear a dress? Did you wear dresses to try and keep your face hidden from Astrid?” 

“No, no, nothing like that. I wore them rather frequently before school, and most children where I am from are put into dresses before they get their more adult clothes when they are older and less prone to ruining them easily.”

Jester pouted slightly, clearly having been looking forward to hearing stories of how Caleb hid his gender and appearance entirely in the years preceding his travels with the Mighty Nein in an attempt to stay hidden from Ikithon and the other Vollstreckers. Still, she carefully pulled the underdress free from the outer layer, shaking it open before opening the back for Caleb to step into. He took a deep breath, looking at the tight sleeves and the rest of the dress before stepping into it, trying not to worry about whether or not it would fit. He knew he was slim, even beyond the fact that he still looked borderline starving, even after the months of travel and regular meals with the other members of the party. 

Caleb helped Jester pull up the dress, and any worries that the sleeves or any of it wouldn’t fit were quickly relieved as he settled the garment onto his shoulders. Jester quickly got to work lacing and tightening the back of the dress, pulling the garment tight around his stomach, the bones shaping his waist to something more narrow than it had been, and a far more elegant shape than he could have naturally hoped for. The skirt was somewhat short, falling just above his knee, but the shape of it looked nice, flaring out from the bottom of the waistband, the embroidery following the lines of the pleating in the center of the skirt. 

“You’re not finished, silly!”

“I know, Jester, but this is rather beautiful, and I would like to see it on me.”

Jester huffed, though she rested her head on his shoulder as he looked at his body in the mirror, and the dress. It really looked beautiful, and he shifted, trying not to fuss over everything, but he wanted to, and he wanted to pick and pull at it, especially with how finely made the fabric and stitching was and how he knew he didn’t deserve to have this even for a moment. 

“You look very nice, Caleb. Now if I could get the overdress onto you?” she asked, a smile teasing at her lips, and Caleb rolled his eyes before nodding, letting Jester start to ease his arms back into the sleeves. 

“How are the sleeves long enough for me? Your arms are much shorter than mine.”

“Oh, they usually bunch up on my arms. That’s how it’s technically supposed to look, but it makes it very convenient when your taller friend wants to try your dresses on so he can look pretty for once.”

“I’ve been assured that I already am pretty when I actually take the time to bathe and not hide my face with mud,” Caleb said, not even thinking until the words came out of his mouth and a blush bloomed across his cheeks. 

“I know. I just like hearing you admit that you’re pretty and kind and a good person and not broken like you always seem to claim,” Jester said, frowning at him in the mirror before settling the overdress on his shoulders and turning to start clasping it closed. 

It closed tight against his throat, and only remained joined until just past his breastbone, curling around his sides to end in two points at his back like a pair of bird’s wings, letting his waist be shown off by the boning and the curl of the embroidery. The sleeves of this part of the dress would end just above his wrist, but the sleeves were rolled back into two large cuffs with birds embroidered where cufflinks would sit if it were a usual shirt or jacket. It looked beautiful on him, almost as though Jester’s dressmaker tailored it to him, and the thought made him pause, narrowing his eyes as he looked at Jester in the mirror. 

“It fits like a glove, Jester. As though it were made for me,” Caleb said, almost suspicious, especially as he realized that it hadn’t been tailored to accommodate any sort of breasts, and especially not Jester’s. He narrowed his eyes at her, and the immensely innocent expression on her face, before she eventually just sighed and shrugged as she looked at him. 

“I just noticed you look at my dresses sometimes. And I thought I could try to get you one as a gift sometime. So I ordered it the last time I was in Nicodranas, and picked it up before we left. I just...thought you could have something nice that you would never buy yourself,” Jester said, frowning as she picked at the sleeve of her own dress. Caleb sniffed softly, looking down at himself and the dress that draped over his body, before he quickly hugged Jester tight. He knew that she had an uncanny insight into their group at this point, but he hadn’t expected it like this at all. He had perhaps expected that she would have figured something out about his past, but not the fact that he had a low-simmering longing to try on her dresses. 

“Thank you, Jester. Do you mind braiding the side of my hair? I think that would look nice,” Caleb said, smiling faintly as he buried his face in her shoulder, still squeezing tight to her. Jester squeezed him back just as tightly, and luckily for him, not as tightly as he knew she could. It felt good, and he finally pulled away a moment later. 

“Of course, silly. I’ve got to make you up all pretty for Fjord and all,” she said, and Caleb blinked, blushing at yet another mention of Fjord, not sure why Jester fixated so much on Fjord in relation to him at all. “Sit down, sit down. I’ll go look for the ribbons and then I’ll braid your hair for you,” she said, and Caleb smiled as he settled down on the ground in front of the bed so that it would be easy for Jester to braid, closing his eyes and leaning his head back against the side of the bed. 

“We will need to get me a pair of stockings at some point. Or leggings. I do not particularly wish to shave my legs just for when I wear a dress.”

“Who says you have to shave?”

“I am just not a fan of hairy legs under skirts. It is…” Caleb shrugged sighing as he opened an eye as he felt Jester settle on the bed behind him. “I just do not like it. I never did when I was younger, and I doubt I still would, but it is more trouble than it is worth.”

Jester nodded before starting to take a brush to his hair, carefully pulling the knots free that had worked their way in over the course of the very busy day. “Caleb, do you mind me asking you a personal question?”

“Hmm?  _ Nein _ , no, Jester. You are free to ask anything. I will answer honestly, or avoid answering.”

“Well, that’s just stupid. I won’t ask if you’re just going to avoid the question.”

“Very well. What is your question, Jester? I will give you an answer.”

A long pause stretched out as Jester continued to brush his hair out, occasionally tossing stray twigs that had lodged into his hair during the trip to Zadash and hadn’t gotten out yet, and Caleb worried that he had somehow said the wrong thing. “You said you used to wear dresses? How come? I thought you said your parents were poor. I don’t...I just know that poorer people don’t usually get the chance to try new clothes very often or do things that people don’t normally get to try.”

“That they’re more conservative and don’t let boys wear dresses much at all?”

Jester’s hands paused before she nodded, claws scraping up against his scalp to start gathering his hair into braids along the side of his scalp. “Yeah. I mean, in Nicodranas it isn’t a big deal, but I thought you were a farmer or something, and the Empire always seems so stuffy.”

“They were. And I was considered a girl for the vast majority of my childhood. Most of it, until I went to the Academy and let myself admit that I wasn’t at all a girl. So, naturally I wore dresses when I was growing up. And because all children wore dresses when I was younger. Easier to clean up and take care of.”

Jester remained silent before pressing a light kiss against Caleb’s scalp before returning to the braids, carefully weaving the ribbon into his hair and being careful not to tug too much. “Why did you stop wearing dresses? You seem to like them now.”

“A number of reasons, though, well…” Caleb shrugged before glancing away. “It is mostly that I was essentially in the military. And a gentleman, or trying to be. I did not have the body of one, not at first, but I could certainly look the part. Unfortunately, dresses did not allow for that. And then I hated myself enough that I did not want to add that hatred of my body on top of it. So I have not allowed myself to really think too much about it, even if your dresses have been tempting.” 

They fell silent after that, Jester dying his hair back with what was left of the length of ribbon that hadn’t already been woven into the braids along the side of his head, and Caleb just relaxed into the soothing motions of having his hair played with and tugged at. It was a pleasant sensation, especially now that mud and dirt and grime wasn’t caked in it, practically matting it and keeping it from being the usual color of a bright copper piece polished by pockets and passage between hands. 

“There we are. You look very pretty, Caleb. If you are okay with that. Very handsome, too,” Jester said, smiling before standing up and helping Caleb to his feet. He smiled at her in return, shrugging before turning to look at himself in the mirror settled in the corner, pausing as he saw the deep green ribbon that matched the underdress in his hair, and then the dress that did fit his body far better than he would have expected. 

“Oh. Oh, Jester.”

“You don’t have to thank me. Just make sure that Fjord sees you, or something like that. Enjoy the dress and wear it as much as you would like. And go dress shopping with me later on. If you want,” Jester said, grinning wide enough to show off her pointed canines, and Caleb couldn’t help the fond smile that spread across his face as he pressed a kiss to her forehead. 

“Thank you so much, Jester. Now, I suppose I have a half-orc to see, if you insist so much.”

“I do. Now shoo! Go see him and knock his socks off,” Jester said, already pushing Caleb out of the door and into the hallway.

**Author's Note:**

> Basically, the small smile on Liam's face was totally Caleb's small smile he always has around Jester when he's indulging her, and I decided to take that and run with it and make it so that Caleb was TOTALLY INTO the idea of wearing a dress for no reason other than they can be comfortable and look pretty when they're made right.   
And, also, Jester's got a fucking 20 wisdom. So I'm leaning hard into that because more people need to realize just how wonderful and insightful she is, and has been, especially since they spent so much time on a boat together. So, obviously, if Caleb wants to wear a dress and has been looking at Jester's dresses with a slight bit of jealousy, she'd totally notice and try to do something nice for him.   
And widofjord in the background because I fucking can. Take that. Ha.   
Hopefully you enjoyed this!


End file.
